Acetic Acid → 4-(4-Dimethylamino-piperidin-1-yl)-benzoic acid

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Reaction Steps

280 mg (1.22 mmol) of 4-(4-dimethylamino-piperidin-1-yl)-benzonitrile (reference example 114a) was dissolved in 2 ml of acetic acid, 4 ml of 6 N HCl was added and the mixture stirred with reflux for 16 h. After cooling 20 ml of water was added and extracted with DCM (3×). The pH of the aqueous phase was adjusted to 5 with KOH pellets, white solid precipitated which was filtered off, washed and dried to give 257 mg of the title compound (85% yield). 1H NMR (CDCl3): δ 7.88 (dd, 2H), 6.98 (dd, 2H), 4.09 (d, 2H), 3.42 (m, 1H), 3.29 (t, 2H), 2.90 (s, 6H), 2.89-2.96 (m, 2H), 2.18 (m, 2H), 1.80 (dq, 2H). MS (ion spray) m/z 249 (M+H)+. 90% pure by analytical HPLC.

Provenance & Evidence